Potassium Nitrate → 4-methyl-7-nitro-3,4-dihydro-2H-isoquinolin-1-one

HRID 1358254Notes

Reaction equation

HRID 1358254 reaction equation
[CH3:1][CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[O:12])[NH:4][CH2:3]1.[N+:13]([O-])([O-:15])=[O:14].[K+]>S(=O)(=O)(O)O>[CH3:1][CH:2]1[C:11]2[C:6](=[CH:7][C:8]([N+:13]([O-:15])=[O:14])=[CH:9][CH:10]=2)[C:5](=[O:12])[NH:4][CH2:3]1

Participants

4

Reactant 2

HCID 24434Potassium NitrateHCID 140400954-Methyl-3,4-dihydroisoquinolin-1(2H)-one

Product 1

HCID 181844524-methyl-7-nitro-3,4-dihydro-2H-isoquinolin-1-one

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

A solution of 4-methyl-3,4-dihydro-2H-isoquinolin-1-one (1. Og) (J. Med. Chem., 1988, 31, 433) in conc. sulfuric acid (5 ml) was added dropwise over 20 min to an ice cooled solution of potassium nitrate (0.678 g) in conc. sulfuric acid (5 ml). The mixture was stirred for a further 30 min with ice-cooling. The mixture was added dropwise to ice (150 g) with stirring. The precipitated solid was collected by filtration, washed with water and dried to give the sub-titl compound (0.95 g). 1H NMR δ: 1.28 (3H, d, J=6.6 Hz), 3.14-3.28 (1H, m), 3.52 (2H, m), 7.67 (1H, d, J=8.5 Hz), 8.29 (1H, s), 8.35 (1H, dd, J=2.5, 8.4 Hz) (1H, d, J=2.5 Hz).

Workup

  1. temperaturecooling
  2. stirringwith stirring
  3. filtrationThe precipitated solid was collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-2c4296ca823b4d7698a6f584b768aea2
Source dataset
uspto-grants-2003_07
Patent number
US06596730B1

Reaction notes

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